Title: Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! Waterfront vacation home with kitchen and patio ![Dining](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008269/78f075db.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Beach nearby](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008269/01952b48.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008269/7b6c6a56.jpg?impolicy=resizecrop&rw=297&ra=fit) ![TV](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008269/cbb08b9e.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008269/cbc930c5.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! provides laundry facilities and more. Active travelers can enjoy kayaking at this vacation home. Stay connected with free in-room WiFi. 10 Exceptional ### Entire home 4 bedrooms2 bathrooms1525 sq ft ## Popular amenities - Parking available - Dryer - Pet-friendly - Washer - Barbecue grill - Kitchen ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! This home is professionally managed by Pretty Picky Properties Spectacular Pleasant Bay Views, Free Boating Bonus! NEW Listing 2025! Rents Friday - Friday in Peak Summer Sleeps Eight Four Bedrooms, Two Baths Linens Included, Beds Made Pets Considered Location If you've ever driven on Route 28 between Chatham and Orleans, you were no doubt struck by the stretch of that road that runs right by beautiful Pleasant Bay. That's the view you get from this property, definitely one of the most scenic water views on all of Cape Cod. Based here, you are only a short drive from the village center of either Orleans or Chatham, each with a wealth of outstanding restaurants, shops and fun activities such band concerts, Cape League baseball, and much, much more. Even closer are the top-notch eateries at Wequassett Resort, including the signature Twenty-Eight Atlantic Restaurant with a Forbes 5-Star rating. If beach time is your idea of a good time, it's only a 1.3-mile drive to sandy Jackknife Cove Beach. But to take advantage of this location's unique appeal, you don't have to drive anywhere. You're right next door to Pleasant Bay Community Boating (locally known as “PBCB”), where boating is king. There are programs and lessons for beginners as well as rentals for sailing veterans. You'll also find programs in marine science education, part of PBCB's community mission. Outside Living Space Given the stunning view from here, you'll no doubt choose to spend most of your time on this cottage's oversized deck where the entire panorama of Pleasant Bay is on display for you. Besides the outdoor seating, you'll find the gas grill out here, as well as the enclosed outdoor shower. The patio offers another attractive outdoor gathering place. Just steps from the cottage, you also have access to a small private beach and an extra-long dock, each of which is shared with PBCB. Inside Living Space The home's main level presents an appealing, open concept floorplan which flows from the fully equipped, updated kitchen with a big gas range into the spacious living room and dining area. This entire space is open, bright and cheery, thanks to a virtual wall of glass showcasing that breathtaking water view. A handsome beamed ceiling adds to the cottage charm. There's a second lounge area here as well. The main level is home to one of the cottage's two full baths, as well as the laundry/pantry, including a full-size spare fridge. Sleeping Accommodations There's one main level bedroom, which has a queen size bed and its own private full bath en suite. The rest of the sleeping is provided on the second level. You'll find a king bedroom, another queen and a third bedroom with a pair of twins. The king and queen bedrooms on the second level have commanding, elevated water views. Sailing Opportunities Offered from mid-June through late August is a private sailing experience. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing. With your stay at Pleasant Bay Community Boating, we would like to offer this at a discounted rate of $115.00.Please reach out to the main office at least three weeks prior to your arrival at info@pbcb.cc or 508-945-7245. Book now to lock in preferred dates Please enter your travel dates in the top right corner of this page for up-to-date pricing. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $215.00 In addition, there are state and local taxes applied to all reservations of 31 days or less that total 14.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It's your vacation. Get Picky! ℠ ## Property amenities ### Beach - Beach nearby ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Microwave - Oven - Refrigerator - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 4 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Bathtub or shower - Hair dryer - Shower - Towels provided ### Living spaces - Dining table - Living room ### Entertainment - TV with cable/satellite channels ### Outdoor areas - Barbecue grill - Patio ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - Pet friendly ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - On the waterfront ### Things to do - Kayak - Birdwatching nearby - Ecotours nearby - Fishing nearby - Golfing nearby - Hiking/biking trails nearby - Kayaking nearby - Sailing nearby - Swimming nearby - Whale watching nearby - Windsurfing nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - First aid kit - Fire extinguisher ### General - Unit size: 1,525 square feet ## Similar properties ![Interior](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008271/8588ea51.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus! Harwich - Kitchen - Washer - Dryer - Pet-friendly 9.6 Exceptional 89 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=113008271&PinnedHotelID=113008271&HadPinnedHotel=true®ionId=-1&adults=2) ![Dining](https://images.trvl-media.com/lodging/34000000/33490000/33490000/33489984/10324cbe.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 5 bedrooms ocean view estate overlooking cape cod bay Orleans - Kitchen - Washer - Dryer - Pet-friendly 9.4 Exceptional 56 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=33489984&PinnedHotelID=33489984&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/34000000/33570000/33562900/33562838/f6142d3a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista! Dennis - Kitchen - Washer - Dryer - Pet-friendly 9.4 Exceptional 117 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=33562838&PinnedHotelID=33562838&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/35000000/34080000/34077800/34077703/92c848a1.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly! West Chatham - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 40 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=34077703&PinnedHotelID=34077703&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21680000/21674600/21674563/76a90ad4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Ocean views Walk to Beach Pet Friendly AC Private Chatham - Kitchen - Washer - Dryer - Pet-friendly 9.8 Exceptional 7 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=21674563&PinnedHotelID=21674563&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113840000/113838400/113838367/03493d53.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Harbor Vista: 003-O Sleek & Modern East Orleans Retreat with Stunning Ocean Views East Orleans - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=113838367&PinnedHotelID=113838367&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/70000000/69330000/69320900/69320836/35103b6d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront on Pleasant Bay! Orleans - Kitchen - Washer - Dryer - Pet-friendly 9.0 Wonderful 12 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=69320836&PinnedHotelID=69320836&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/24000000/23290000/23280900/23280855/e7b28cd0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Secluded Chatham Cape Cod House Stage Harbor Area Chatham - Kitchen - Washer - Dryer - Pet-friendly 9.8 Exceptional 46 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=23280855&PinnedHotelID=23280855&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104280000/104274300/104274207/ebf52524.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront Home With Dock and Two Water Facing Decks! (2372) Chatham - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=104274207&PinnedHotelID=104274207&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/54000000/53340000/53332300/53332210/af56bc23.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Stylish Orleans home with spacious deck - near bay & ocean beach Orleans - Kitchen - Washer - Dryer - Air conditioning 8.4 Very good 40 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=53332210&PinnedHotelID=53332210&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Contactless check-in available ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Pets Pets allowed Service animals are welcome, and are exempt from fees ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher and a first aid kit This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation Property Registration Number C0257282240 ### Property is also known as 942738 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C41.72945%2C-69.99189&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=GjVADa-neA28fJXD6D13syDlpGQ=) Orleans, MA #### What's nearby - Nickerson State Park - 7 min drive - 5.3 km - Chatham Fish Pier - 7 min drive - 9.5 km - Chatham Lighthouse - 10 min drive - 10.5 km - Skaket Beach - 11 min drive - 9.8 km - Ocean Edge Golf Club - 11 min drive - 9.2 km #### Getting around - Hyannis Transportation Center - 25 min drive - Hyannis, MA (HYA-Barnstable Municipal) - 31 min drive #### Restaurants - ‪Three Fins Coffee House & Cacao Factory - ‬6 min drive - ‪Dunkin' - ‬4 min drive - ‪Pain D'avignon - ‬6 min drive - ‪Hangar B Eatery - ‬7 min drive - ‪400 East - ‬4 min drive ## Frequently asked questions ### Is Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! pet-friendly? > Yes, pets are allowed at this property. ### Where is Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! located? > Situated on the waterfront, this vacation home is within 2 mi (3 km) of Cape Cod Beaches, Captain's Cove Golf Course, and Captains Golf Course. Caleb Nickerson House and Chatham Marconi Maritime Center are also within 3 mi (5 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! Reviews 10 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 4 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Cleanliness ### 10/10 Excellent #### Terry W. Oct 7, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy The views from the house were wonderful and the beach in front of the house was perfect. The house is located in the perfect spot. We are planning to go back next year. ##### Terry W. Stayed 7 nights in Sep 2025 ### 10/10 Excellent #### Ted O. Sep 24, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Amazing location. Lots of natural light. Would love to stay here again! ##### Ted O. Stayed 3 nights in Sep 2025 ### 10/10 Excellent #### Daniela L. Jun 9, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy We really enjoyed our stay. The location was convenient and the views from the property were exactly what we needed. We had a few minor issues during our stay that were quickly and professionally addressed by the management team. ##### Daniela L. Stayed 4 nights in May 2025 ### 10/10 Excellent #### Sarah L. Jun 20, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy ##### Sarah L. Stayed 3 nights in May 2025 ## Expedia's Latest Trends ### Hotels > [Silver Reef Casino Resort](https://www.expedia.ca/Bellingham-Hotels-Silver-Reef-Casino-Resort.h16231932.Hotel-Information) > > [The Trail in Adams - Berkshires’ Art Hotel](https://www.expedia.ca/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information) > > [Great Wolf Lodge Boston / Fitchburg, MA](https://www.expedia.ca/Leominster-Hotels-Great-Wolf-Lodge-Boston-Fitchburg.h8458771.Hotel-Information) > > [Comfort Inn Hyannis - Cape Cod](https://www.expedia.ca/Hyannis-Hotels-Comfort-Inn.h1240460.Hotel-Information) > > [The Corsair & Cross Rip Oceanfront Resort](https://www.expedia.ca/Dennis-Port-Hotels-The-Corsair-Cross-Rip-Oceanfront-Resort.h894158.Hotel-Information) > > [Harbor Hotel Provincetown](https://www.expedia.ca/Provincetown-Hotels-Harbor-Hotel-Provincetown.h421590.Hotel-Information) > > [Freebird Motor Lodge by Reverie Boutique Collection](https://www.expedia.ca/West-Yarmouth-Hotels-Hunters-Green-Cape-Cod.h6589307.Hotel-Information) > > [La Quinta Inn & Suites by Wyndham Boston-Andover](https://www.expedia.ca/Andover-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Boston-Andover.h25755.Hotel-Information) > > [Chatham Bars Inn](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) > > [Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) > > [Hyannis Travel Inn](https://www.expedia.ca/Hyannis-Hotels-Hyannis-Travel-Inn.h1379109.Hotel-Information) > > [Hyatt Place Marlborough/Apex Center](https://www.expedia.ca/Worcester-Hotels-Hyatt-Place-MarlboroughApex-Center.h20178059.Hotel-Information) > > [Best Western Cape Cod Hotel](https://www.expedia.ca/Hyannis-Hotels-Best-Western-Cape-Cod-Hotel.h28183.Hotel-Information) > > [Best Western Royal Plaza Hotel & Trade Center](https://www.expedia.ca/Worcester-Hotels-Best-Western-Royal-Plaza-Hotel-Trade-Center.h14628.Hotel-Information) > > [Cape Cod Family Resort and Parks](https://www.expedia.ca/West-Yarmouth-Hotels-Cape-Cod-Family-Resort-And-Inflatable-Park.h5306790.Hotel-Information) > > [Brass Key Guesthouse - Adults Only](https://www.expedia.ca/Provincetown-Hotels-Brass-Key-Guesthouse-Adults-Only.h18632862.Hotel-Information) > > [Club Wyndham Bentley Brook](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information) > > [Tulalip Resort Casino](https://www.expedia.ca/Everett-Hotels-Tulalip-Resort-Casino.h2161524.Hotel-Information) > > [Sea Crest Beach Resort](https://www.expedia.ca/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.Hotel-Information) > > [Northside Motel](https://www.expedia.ca/Williamstown-Hotels-Northside-Motel.h1581984.Hotel-Information) > > [Six Flags Great Escape Lodge & Indoor Waterpark](https://www.expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) > > [Darien Lake Lodge on the Lake](https://www.expedia.ca/Corfu-Hotels-Darien-Lake-Lodge-On-The-Lake.h13279584.Hotel-Information) > > [Holiday Inn Express Boston - Milford by IHG](https://www.expedia.ca/Milford-Hotels-Holiday-Inn-Express-Boston-Milford.h555108.Hotel-Information) > > [Bayside Resort Hotel](https://www.expedia.ca/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) > > [Canad Inns Destination Center Grand Forks](https://www.expedia.ca/Grand-Forks-Hotels-Canad-Inns-Destination-Center-Grand-Forks.h1713856.Hotel-Information) > > [JW Marriott Desert Springs Resort & Spa](https://www.expedia.ca/Palm-Springs-Hotels-JW-Marriott-Desert-Springs-Resort-Spa.h17123.Hotel-Information) > > [Residence Inn By Marriott Boston Andover](https://www.expedia.ca/Andover-Hotels-Residence-Inn-By-Marriott-Boston-Andover.h795379.Hotel-Information) > > [Embassy Suites by Hilton Boston Marlborough](https://www.expedia.ca/Worcester-Hotels-Embassy-Suites-By-Hilton-Boston-Marlborough.h22959.Hotel-Information) > > [SpringHill Suites by Marriott Wrentham Plainville](https://www.expedia.ca/Wrentham-Hotels-SpringHill-Suites-By-Marriott-Wrentham-Plainville.h57749189.Hotel-Information) > > [The Brook at Turning Stone Resort Casino](https://www.expedia.ca/Utica-Hotels-Turning-Stone-Resort-And-Casino.h1684407.Hotel-Information)